Day 3 · Asking Better Questions - The Art of Elicitation
Reaching the knowledge stakeholders cannot reach themselves
The most valuable thing a stakeholder knows is usually the thing they will never think to tell you. Not because they are hiding it, but because they have forgotten they know it. Expertise has a strange side effect. The better someone gets at a job, the more of it sinks below the surface of their attention, until the hardest, most skilful parts of what they do feel like nothing at all. Ask them to explain it, and they hand you the simple version they believe is true, and the real work, the judgment that took them ten years to build, stays underwater.
There is a name for this. Tacit knowledge. The knowing that lives in the hands and the gut rather than in words. A baker who can tell by feel when the dough is ready cannot write you the rule, because there is no rule; there is a thousand loaves of experience compressed into a touch. Most of the people you elicit from are carrying knowledge like that about their own work, and if you only ask questions, you will only ever get the part they can say out loud.
Why the tidy answer is always wrong
When you ask someone to describe their process, they describe the happy path. The clean version, where everything goes right. They do this because the happy path is the version that lives in words, and the exceptions, which are where almost all the real complexity sits, are handled by reflex and never make it into the explanation. So you build the happy path. It works in the demo and falls apart in week one, when the first real order arrives with a missing field, a duplicate, a customer who is also a supplier, a situation the expert handles without thinking and forgot to mention because to them it is not an exception at all, it is just Tuesday. The gap between the tidy answer and the real work is not a small gap. It is most of the job. Your task is to get into it.
Go and watch
The single highest-value thing you can do is stop asking and start watching. Sit beside the person while they do the actual work, on real cases, and say almost nothing. This is sometimes called contextual inquiry, and the dull name hides how powerful it is. You are not interviewing the work as remembered. You are observing the work as done, and the difference between those two is where every hidden requirement lives. When you watch, the eleven invisible judgements become visible. You see the hesitation before they approve a certain kind of order. You see them open a second screen that they never mentioned. You see them ignore the official process for a faster one that everybody actually uses. And now you can ask about the specific thing in front of you, which is a hundred times easier to answer than a question asked in the abstract. "You paused there. What were you checking?" is a question the expert can answer, because the moment is right in front of them. "What do you check before approving" in a meeting room is a question they will answer wrongly, with the tidy version.
Techniques that pull the hidden into the open
When you cannot watch, or to go deeper when you can, a handful of question moves do reliable work. They share a logic. Instead of asking for the rule, you ask for the situation and let the rule reveal itself.
Ask for the last time, not the usual time
"Tell me about the last refund that was a headache" beats "how do refunds work." The specific recent story drags the exceptions into the open, because the headache was the exception. General questions get general answers. Specific stories get the truth.
Hunt the exceptions on purpose
"When does this not work the normal way?" and "What is the weirdest case you have ever had to handle?" Experts light up at these, because the strange cases are the ones they are quietly proud of surviving. And the strange cases are your requirements.
Ladder from the what to the why
When they tell you they always do something, ask why, then ask why again. "I always flag orders over a certain value." Why? "Because they need a second pair of eyes." Why? "Because we got burned once." Three whys in, you have moved from a rule to the reason behind it, and reasons are far more useful than rules because they tell you when the rule should bend.
Use contrast to find the edges
"How is a rush order different from a normal one?" Difference questions expose the branching logic people carry without naming. Every "it depends" they give you is a rule waiting to be written down.
Listen for the gap, not just the words
The advanced version of this is learning to hear what is missing. When someone describes a process and never once mentions what happens when something fails, that silence is a finding, not a gap to ignore. When two people describe the same step using different words, the difference is telling you they do not actually agree, even though they think they do. When someone says "usually" or "normally" or "most of the time," they have just pointed at an exception and walked past it. Walk back to it. "You said usually. When is it not usual?"
These qualifier words, usually, normally, mostly, typically, generally, are gifts. They are the stakeholder's own subconscious flagging the place where the tidy story breaks down. Train your ear to catch them the way an editor catches a typo, and follow every single one. Most of your best requirements are hiding directly behind the word "usually."
Why is this the part that travels furthest
Surfacing what someone cannot say is the deep version of a skill every good professional has. A great teacher draws understanding out of a student who could not have asked for it. A good manager learns why someone is really leaving, not the reason on the resignation letter. A skilled interviewer gets past the rehearsed answer to the real one. The technique changes with the setting. The art is the same. You are reaching for knowledge that the other person cannot hand you directly, and you are doing it with patience rather than cleverness.
If you are a beginner, you can take one technique from today, the last time question, and you will immediately get better answers. A senior reading this is nodding because they learned years ago that the tidy answer is a trap, and they have their own collection of moves for getting underneath it. Tomorrow, the challenge changes shape again. We leave the quiet one-to-one and walk into a room full of people, where the problem is no longer drawing one person out but stopping six people from turning the session into noise.
Go out and be successful.
Oluwatosin Ogunkoya | Flotog BA Insights | www.flotogbainsights.com
Tomorrow: Running a Room That Produces Answers
Facilitation, the loud and the silent, and how to keep a workshop from becoming noise.